


Pretty Boy

by princesssroyalpinkpanties



Series: Tumblr prompts [7]
Category: Supernatural
Genre: Fluff, M/M, Sam in dresses, Smut
Language: English
Status: Completed
Published: 2017-03-10
Updated: 2017-03-10
Packaged: 2018-10-02 06:47:10
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 503
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10211915
Author URL: https://archiveofourown.org/users/princesssroyalpinkpanties/pseuds/princesssroyalpinkpanties
Summary: Prompts: Sammy likes to wear dresses and feels pretty with them





	

The first time he thought about it, Sam was 13. Dean had found a poster of Marilyn Monroe with that classic pose with her dress flowing around her and kept it above his bed for the time period they’d stayed at the motel on some nameless town. Sam looked at the beautiful woman, her big smile, pretty hair and long legs showing beneath the gorgeous dress; then Sam watched Dean and the way he looked at that poster and wanted to look pretty for his brother, too.

When he turned 17 and his body was already grown, just like his feelings for his brother, Sam bought his first real dress. It fitted his lean torso perfectly, satin falling softly from the waist down. Sam looked himself in the mirror, so afraid of how he’d look and how stupid he would feel, but the image on the mirror was nothing but delicate. Sam smiled and twirled, loving how the dress moved and how it felt good on his skin.

Sam kept staring at his image, smiling and feeling confident. He saw Dean watching him from the corner of his eye, but didn’t stopped. Instead, he smiled wider, drinking of his big brother’s lust for him. Dean asked him about the dress a week later, between soft kisses and sweet talk. That night, he wore the dress for Dean and rejoiced when his brother lost control of himself because he was wearing a dress.

“You’re prettier than all those girls, baby boy. Fuck, can’t believe you’re all mine, dressing like that for me.” Dean whispered between the thrusts of his hip.  Sam moaned his agreement and didn’t took off the dress while Dean was fucking him.

Sam kept that dress for years, sometimes he would wear it at Stanford, before he met Jessica and needed something to remind him he was still Dean’s pretty brother. That he had not lose him completely.

Dean bought him a new dress for the Valentine’s Day they’d spent in the bunker. Sam wore it that night again and watched as Dean lost control of himself just the same. They still could be like horny teenagers sometimes.

Sometimes Dean would get home from a long supplies run and find Sam walking through the bunker wearing only his dress, comfortable and loose. That always ended with him fucking Sam on the library table, the kitchen counter or even on top of one of the cars on the garage. Sam loved how powerful and sexy Dean made him feel just because of a piece of clothing.

“Hey! Careful with it, Dean. Don’t ruin my dress or you’ll have to buy another.” Sam gasped when Dean pushed him against the wall of the hallway. Dean chuckled, but his touch was more careful after. He mouthed Sam’s nipple through the fabric and traced his lips up, till they found Sam’s own. Sam gave himself up to his brother’s touch.

“Don’t worry, Sammy. I’ll buy all the dresses in the world for my pretty boy.”


End file.
